Butyl 12-ketostearate



Patented Jan. 7, 1941 UNITED STATES PATENT OFFICE 2,227,823 Burn. IZ-KETOSTEARATE Henry L. South Charleston, W. Va., assignor, by mesne assignments, to Union Carbideand Carbon Corporation, a corporation or New York No Drawing. Original application June 7, 1934, Serial No. 729,442, now Patent No. 2,180,730,

dated November 21, 1939.

Divided and this application December 10, 1938, Serial No. 244,924

1 Claim.

- CH3(CH2) 5CH(OH) (CH2) COOH which in turn can be synthesized from castor oil. Castor oil consists chiefly of the glyceride oi 'ricinoleic acid, or triricinolein, which when hydrogenated, saponiiied with sodium hydroxide, and then hydrolyzed with acid, will yield the above hydroxystearic acid. By further treatment of this acid with chromic acid, or other oxidizing agent, a carbonyl group is formed at the 12 position of the molecule, and the resulting product is 12- ketostearic acid. By reaction with butyl alcohol, an ester of this ketostearic acid maybe formed.

As illustrative of the manner or preparing the l2-ketostearic acid, and the ester, the following examples are given:

Example 1 Castor oil was treated in the manner previously indicated, and a quantity. of 12-hydroxystearic acid was obtained and identified by its known properties. 150 grams of this hydroxystearic acid was dissolved in 250 grams of acetic acid. with constant stirring a mixture of 30 grams of chromic acid (010:) in 500 grams of acetic acid was gradually added at a temperature of 30 to 35 C. After the reaction was complete, the whole was poured into several volumes of water, and a 'crude product crystallizedout.

Thiswas dissolved in methanol, again precipitated with water, 5 and then dried. A final yield of 120 grams was obtained, which had an acetyl number of substantially zero, and an equivalent weight and other properties indicating the product l2-ketostearic acid, which may be represented by the 10 structural formula CHs-(CH:) s-CO-(CHz) 1o--COOH Example 2 Butanol in an excess of one mol was heated 15 with l2-ketostearic acid in the presence of catalytic proportions of sulfuric acid. After completion oi the reaction the mixture was neutralized with a dilute sodium hydroxide solution and distilled.

The fraction distilling at 208 to 212 C. at 2 mm.

pressure was collected. This product was identified from its equivalent weight and other prop-' erties as butyl l2-ketcstearate. It was a wax-like solid having a meltingpoint of 56 0., and the probable structural formula CHr-(CHa) s-CO-(CH2) iii-COOCiHt The invention should not be limited other than as defined in the appended claim. This application is a division of my copending application Serial No. 729,442, filed June 7, 1934, now Patent I claim: Butyl iz-ketostearate.

HENRY L. co'x. 

